A Review of Advances in the Synthesis of Analogues of the Delphinium ­Alkaloid Methyllycaconitine

Abstract

Neuronal nicotinic acetylcholine receptors of the a7 subtype are potential targets for drug development in the treatment of Alzheimer's disease. The Delphinium alkaloid methyllycaconitine is a potent and selective a7 sub-type selective nicotinic acetylcholine receptor antagonist. The total synthesis of this pharmacologically active alkaloid has not yet been achieved. A summary of semisynthetic methods to prepare methyllycaconitine is presented. Existing synthetic strategies used to prepare E, AE, AEF, ABE, ABDE, ABEF ring analogues of methyllycaconitine are reviewed for the first time.

A concise and stereoselective synthesis of the BCDF tetracyclic ring system of C19-diterpenoid alkaloids

“…Their intricate structures and diverse biological activities have attracted considerable attention from synthetic chemists over the past ve decades. 5 As pioneers in the eld, Wiesner et al developed four generations of fundamental synthetic strategies for the practical synthesis of talatisamine, chasmanine, and 13-desoxydelphonine in the 1970s. 6 In the last decade, research groups led by Gin, 7 Sarpong, 8 Fukuyama, 9 Inoue 10 and Reisman 11 have made signicant contributions, culminating in the elegant total syntheses of weisaconitine D, liljestrandinine, cardiopetaline, talatisamine and puberuline C.…”

Construction of the tetracyclic ring system of diterpene alkaloids via cationic [5 + 2] cycloaddition

“…Herein, we disclose the results of our synthetic study on diterpene alkaloids via [5 + 2] cycloaddition. 6–8…”